#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/08/2220898.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220898
loop_
_publ_author_name
'Cui, Jian-lan'
'Duan, Mei'
'Cai, Liu-qing'
_publ_section_title
;
 3,6-Dibromo-9-(4-chlorobenzyl)-9H-carbazole
;
_journal_coeditor_code           RN2052
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o215
_journal_paper_doi               10.1107/S1600536808042815
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H12 Br2 Cl N'
_chemical_formula_moiety         'C19 H12 Br2 Cl N'
_chemical_formula_sum            'C19 H12 Br2 Cl N'
_chemical_formula_weight         449.57
_chemical_melting_point_gt       451
_chemical_melting_point_lt       452
_chemical_name_systematic
;
3,6-Dibromo-9-(4-chlorobenzyl)-9H-carbazole
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.7673(18)
_cell_length_b                   16.732(3)
_cell_length_c                   21.574(4)
_cell_measurement_reflns_used    5270
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.940
_cell_measurement_theta_min      2.435
_cell_volume                     3164.8(10)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18205
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.289
_exptl_absorpt_correction_T_max  0.9016
_exptl_absorpt_correction_T_min  0.7420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.528
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0488P)²+2.2242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                2369
_reflns_number_total             2794
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rn2052.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2220898
_cod_database_fobs_code          2220898
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.22114(6) 0.09041(3) 0.56121(2) 0.02566(18) Uani d . 1 . .
Br Br2 0.65417(6) -0.19402(3) 0.84401(2) 0.02964(19) Uani d . 1 . .
Cl Cl1 0.54034(14) 0.40983(8) 0.94634(5) 0.0248(3) Uani d . 1 . .
N N1 0.2015(4) 0.0764(3) 0.83555(17) 0.0200(9) Uani d . 1 . .
C C1 0.1896(5) 0.0868(3) 0.7726(2) 0.0181(10) Uani d . 1 . .
C C2 0.1017(5) 0.1422(3) 0.7406(2) 0.0205(11) Uani d . 1 . .
H H2 0.0388 0.1783 0.7611 0.025 Uiso calc R 1 . .
C C3 0.1123(5) 0.1410(3) 0.6772(2) 0.0208(11) Uani d . 1 . .
H H3 0.0562 0.1771 0.6536 0.025 Uiso calc R 1 . .
C C4 0.2067(5) 0.0860(3) 0.6482(2) 0.0193(11) Uani d . 1 . .
C C5 0.2911(5) 0.0299(3) 0.6790(2) 0.0193(11) Uani d . 1 . .
H H5 0.3511 -0.0071 0.6580 0.023 Uiso calc R 1 . .
C C6 0.2827(5) 0.0308(3) 0.7433(2) 0.0163(10) Uani d . 1 . .
C C7 0.3559(5) -0.0160(3) 0.7902(2) 0.0170(10) Uani d . 1 . .
C C8 0.4580(5) -0.0795(3) 0.7888(2) 0.0198(11) Uani d . 1 . .
H H8 0.4890 -0.1020 0.7515 0.024 Uiso calc R 1 . .
C C9 0.5117(6) -0.1080(3) 0.8443(2) 0.0236(12) Uani d . 1 . .
C C10 0.4625(5) -0.0769(3) 0.9006(2) 0.0240(12) Uani d . 1 . .
H H10 0.4999 -0.0977 0.9375 0.029 Uiso calc R 1 . .
C C11 0.3590(5) -0.0155(3) 0.9018(2) 0.0224(11) Uani d . 1 . .
H H11 0.3259 0.0052 0.9395 0.027 Uiso calc R 1 . .
C C12 0.3041(5) 0.0154(3) 0.8466(2) 0.0182(11) Uani d . 1 . .
C C13 0.1391(6) 0.1292(3) 0.8828(2) 0.0230(12) Uani d . 1 . .
H H13A 0.1194 0.0985 0.9201 0.028 Uiso calc R 1 . .
H H13B 0.0425 0.1505 0.8683 0.028 Uiso calc R 1 . .
C C14 0.2447(5) 0.1977(3) 0.8982(2) 0.0190(11) Uani d . 1 . .
C C15 0.2722(5) 0.2589(3) 0.8562(2) 0.0208(11) Uani d . 1 . .
H H15 0.2264 0.2568 0.8174 0.025 Uiso calc R 1 . .
C C16 0.3654(5) 0.3226(3) 0.8703(2) 0.0198(11) Uani d . 1 . .
H H16 0.3825 0.3628 0.8414 0.024 Uiso calc R 1 . .
C C17 0.4333(5) 0.3259(3) 0.9281(2) 0.0220(11) Uani d . 1 . .
C C18 0.4101(6) 0.2650(3) 0.9700(2) 0.0237(11) Uani d . 1 . .
H H18 0.4579 0.2666 1.0084 0.028 Uiso calc R 1 . .
C C19 0.3168(5) 0.2020(3) 0.9553(2) 0.0214(11) Uani d . 1 . .
H H19 0.3018 0.1614 0.9841 0.026 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C12 . . 108.3(4) ?
C1 N1 C13 . . 126.0(4) ?
C12 N1 C13 . . 124.9(4) ?
N1 C1 C2 . . 128.2(4) ?
N1 C1 C6 . . 108.6(4) ?
C2 C1 C6 . . 123.2(4) ?
C3 C2 C1 . . 116.7(5) ?
C3 C2 H2 . . 121.7 ?
C1 C2 H2 . . 121.7 ?
C2 C3 C4 . . 119.9(5) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C5 C4 C3 . . 124.1(4) ?
C5 C4 Br1 . . 118.3(4) ?
C3 C4 Br1 . . 117.6(4) ?
C4 C5 C6 . . 116.6(5) ?
C4 C5 H5 . . 121.7 ?
C6 C5 H5 . . 121.7 ?
C5 C6 C1 . . 119.5(4) ?
C5 C6 C7 . . 132.5(5) ?
C1 C6 C7 . . 108.1(4) ?
C8 C7 C12 . . 120.9(4) ?
C8 C7 C6 . . 133.9(4) ?
C12 C7 C6 . . 105.3(4) ?
C9 C8 C7 . . 118.0(5) ?
C9 C8 H8 . . 121.0 ?
C7 C8 H8 . . 121.0 ?
C8 C9 C10 . . 121.7(5) ?
C8 C9 Br2 . . 119.0(4) ?
C10 C9 Br2 . . 119.3(4) ?
C11 C10 C9 . . 120.2(5) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C10 C11 C12 . . 119.6(5) ?
C10 C11 H11 . . 120.2 ?
C12 C11 H11 . . 120.2 ?
N1 C12 C11 . . 130.7(4) ?
N1 C12 C7 . . 109.7(4) ?
C11 C12 C7 . . 119.6(5) ?
N1 C13 C14 . . 112.6(4) ?
N1 C13 H13A . . 109.1 ?
C14 C13 H13A . . 109.1 ?
N1 C13 H13B . . 109.1 ?
C14 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.8 ?
C19 C14 C15 . . 117.5(5) ?
C19 C14 C13 . . 121.0(5) ?
C15 C14 C13 . . 121.5(4) ?
C16 C15 C14 . . 122.0(4) ?
C16 C15 H15 . . 119.0 ?
C14 C15 H15 . . 119.0 ?
C15 C16 C17 . . 119.1(5) ?
C15 C16 H16 . . 120.5 ?
C17 C16 H16 . . 120.5 ?
C18 C17 C16 . . 119.9(5) ?
C18 C17 Cl1 . . 122.1(4) ?
C16 C17 Cl1 . . 118.0(4) ?
C19 C18 C17 . . 120.4(5) ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C18 C19 C14 . . 121.2(5) ?
C18 C19 H19 . . 119.4 ?
C14 C19 H19 . . 119.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C4 . 1.883(4) ?
Br2 C9 . 1.905(5) ?
Cl1 C17 . 1.734(5) ?
N1 C1 . 1.373(6) ?
N1 C12 . 1.382(6) ?
N1 C13 . 1.455(6) ?
C1 C2 . 1.390(7) ?
C1 C6 . 1.393(7) ?
C2 C3 . 1.370(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.387(7) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.368(7) ?
C5 C6 . 1.389(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.431(7) ?
C7 C8 . 1.390(7) ?
C7 C12 . 1.402(6) ?
C8 C9 . 1.371(6) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.390(7) ?
C10 C11 . 1.370(7) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.384(6) ?
C11 H11 . 0.9300 ?
C13 C14 . 1.510(7) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C19 . 1.386(7) ?
C14 C15 . 1.389(7) ?
C15 C16 . 1.377(7) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.383(6) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.376(7) ?
C18 C19 . 1.372(7) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 N1 C1 C2 . . . . -178.9(5) ?
C13 N1 C1 C2 . . . . -8.9(8) ?
C12 N1 C1 C6 . . . . 1.3(5) ?
C13 N1 C1 C6 . . . . 171.2(4) ?
N1 C1 C2 C3 . . . . 178.8(5) ?
C6 C1 C2 C3 . . . . -1.3(7) ?
C1 C2 C3 C4 . . . . 0.4(7) ?
C2 C3 C4 C5 . . . . 1.2(8) ?
C2 C3 C4 Br1 . . . . -177.8(4) ?
C3 C4 C5 C6 . . . . -1.8(7) ?
Br1 C4 C5 C6 . . . . 177.2(3) ?
C4 C5 C6 C1 . . . . 0.8(7) ?
C4 C5 C6 C7 . . . . -178.1(5) ?
N1 C1 C6 C5 . . . . -179.4(4) ?
C2 C1 C6 C5 . . . . 0.7(7) ?
N1 C1 C6 C7 . . . . -0.2(5) ?
C2 C1 C6 C7 . . . . 179.9(4) ?
C5 C6 C7 C8 . . . . -1.5(9) ?
C1 C6 C7 C8 . . . . 179.5(5) ?
C5 C6 C7 C12 . . . . 178.2(5) ?
C1 C6 C7 C12 . . . . -0.9(5) ?
C12 C7 C8 C9 . . . . -2.9(7) ?
C6 C7 C8 C9 . . . . 176.7(5) ?
C7 C8 C9 C10 . . . . 2.3(7) ?
C7 C8 C9 Br2 . . . . -179.1(4) ?
C8 C9 C10 C11 . . . . -0.8(8) ?
Br2 C9 C10 C11 . . . . -179.4(4) ?
C9 C10 C11 C12 . . . . -0.1(7) ?
C1 N1 C12 C11 . . . . 177.3(5) ?
C13 N1 C12 C11 . . . . 7.2(8) ?
C1 N1 C12 C7 . . . . -1.8(5) ?
C13 N1 C12 C7 . . . . -171.9(4) ?
C10 C11 C12 N1 . . . . -179.6(5) ?
C10 C11 C12 C7 . . . . -0.5(7) ?
C8 C7 C12 N1 . . . . -178.6(4) ?
C6 C7 C12 N1 . . . . 1.7(5) ?
C8 C7 C12 C11 . . . . 2.1(7) ?
C6 C7 C12 C11 . . . . -177.6(4) ?
C1 N1 C13 C14 . . . . -85.7(6) ?
C12 N1 C13 C14 . . . . 82.7(6) ?
N1 C13 C14 C19 . . . . -111.0(5) ?
N1 C13 C14 C15 . . . . 69.5(6) ?
C19 C14 C15 C16 . . . . -1.0(7) ?
C13 C14 C15 C16 . . . . 178.4(4) ?
C14 C15 C16 C17 . . . . -0.2(7) ?
C15 C16 C17 C18 . . . . 1.6(7) ?
C15 C16 C17 Cl1 . . . . -176.0(4) ?
C16 C17 C18 C19 . . . . -1.7(8) ?
Cl1 C17 C18 C19 . . . . 175.8(4) ?
C17 C18 C19 C14 . . . . 0.4(8) ?
C15 C14 C19 C18 . . . . 1.0(7) ?
C13 C14 C19 C18 . . . . -178.5(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126633
